Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 88350445, compound

HRID 1584837Notes

Reaction equation

HRID 1584837 reaction equation
C([N+]1(C)CCCC1)C=C.[NH2:10][C:11]1[S:15][N:14]=[C:13](/[C:16](=[N:20]/[O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)/[C:17]([O-:19])=O)[N:12]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.FC(F)(F)C(O)=O.[NH2:58][C@@H:59]1[C:66](=[O:67])[N:65]2[C@@H:60]1[S:61][CH2:62][C:63](/[CH:71]=[C:72]1/[C:73](=[O:96])[N:74]([CH2:77][C:78]3[CH:83]=[CH:82][N+:81]([CH2:84][C:85](=[O:95])[NH:86][C:87]4[CH:92]=[CH:91][C:90]([OH:93])=[C:89]([F:94])[CH:88]=4)=[CH:80][CH:79]=3)[CH2:75][CH2:76]/1)=[C:64]2[C:68]([O-:70])=[O:69]>CN(C=O)C>[NH2:10][C:11]1[S:15][N:14]=[C:13](/[C:16](=[N:20]/[O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)/[C:17]([NH:58][C@@H:59]2[C:66](=[O:67])[N:65]3[C@@H:60]2[S:61][CH2:62][C:63](/[CH:71]=[C:72]2/[C:73](=[O:96])[N:74]([CH2:77][C:78]4[CH:79]=[CH:80][N+:81]([CH2:84][C:85](=[O:95])[NH:86][C:87]5[CH:92]=[CH:91][C:90]([OH:93])=[C:89]([F:94])[CH:88]=5)=[CH:82][CH:83]=4)[CH2:75][CH2:76]/2)=[C:64]3[C:68]([O-:70])=[O:69])=[O:19])[N:12]=1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15839930HCID 15839930, compoundHCID 86754391HCID 86754391, compound

Product 1

HCID 88350445HCID 88350445, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (Z)-(5-amino-[1,2,4]thiadiazol-3-yl)-cyclopentyloxyimino-acetate 1-allyl-1-methyl-pyrrolidinium salt in 10 ml DMF was treated with HBTU (170 mg, 0.45 mmol) for 1.5 h at room temperature. (E)-(6R,7R)-7-Amino-3-[1-[1-[(3-fluoro-4-hydroxy-phenylcarbamoyl)-methyl]-pyridin-1-ium-4-ylmethyl]-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate trifluoroacetic acid salt (300 mg, 0.45 mmol) was added and the mixture was stirred for 78 h before it was concentrated in vacuo. The residue was dissolved in ethylacetate and extracted with water. The organic phase was evaporated and the residue triturated with diethylether. The product was purified by gel chromatography (MCI-gel, using a gradient of water with increasing concentrations of acetonitrile). Yield: 40 mg (11%).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethylacetate
  3. extractionextracted with water
  4. customThe organic phase was evaporated
  5. customthe residue triturated with diethylether
  6. customThe product was purified by gel chromatography (MCI-gel
  7. temperaturewith increasing concentrations of acetonitrile)

Sources & evidence

ORD record
ord-5116797e116c4ea0ac7ddd13e04f958a
Source dataset
uspto-grants-1999_08
Patent number
US05935950

Reaction notes

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